Gwen Sissymittens

Last Activity:: Apr 27, 2024 at 12:26 AM

Joined:: Jan 8, 2023 at 4:34 AM

Messages:: 113

Likes Received:: 674

Trophy Points:: 103

Albums:: 3

Photos:: 25

Local Time:: 3:20 AM

Following 47

Followers 40

Gender:: Male

Gwen Sissymittens

Active member, Male

I’m coming up on my fourth day in my chastity cage. I’m trying to break my record of five days without removal. Apr 27, 2024 at 12:26 AM

Gwen Sissymittens was last seen:: Apr 27, 2024 at 12:26 AM

1. Gwen Sissymittens
  I’m coming up on my fourth day in my chastity cage. I’m trying to break my record of five days without removal.
  
  Apr 27, 2024 at 12:26 AM
2. Gwen Sissymittens
  Finally back home from vacation. Wearing black nightgown, thong, and high steel slave collar!
  
  Apr 15, 2024
  
  Teagirl, Stephplayswithyou, Lisa4343 and 1 other person like this.
3. Gwen Sissymittens
  Last night my wife put me in the corner for asking a question during her TV show. Very unexpected and very hot!
  
  Mar 26, 2024
  
  Gregor and Goddess Jade like this.
  1. Goddess Jade
    VERY, I concur! x
    
    Mar 27, 2024
    
    Gwen Sissymittens likes this.
4. LoriB
  Post a picture you going out, you must have one ❤️
  
  Feb 25, 2024
  
  Teagirl and Gwen Sissymittens like this.
5. LoriB
  Don't worry about those idiots. The important thing you felt amazing
  . Practice with makeup and poise will make you fit in as a beautiful woman
  
  Feb 25, 2024
  
  Gwen Sissymittens likes this.
6. LoriB
  So happy for you, hope you post beautiful picture of yourself. It will be so much fun and fulfilling.
  Good luck sweetie
  
  Feb 25, 2024
  1. Gwen Sissymittens
    It wasn’t great. I got laughed at.
    
    Feb 25, 2024
  2. Teagirl
    You're so pretty! Fuck those haters.
    
    Mar 16, 2024
    
    Gwen Sissymittens likes this.
7. Gwen Sissymittens
  I’m going out dressed in public for the first time! Wish me luck!!!
  
  Feb 24, 2024
  
  Teagirl, Stephplayswithyou, anasyrma and 4 others like this.
  1. Rimmer69
    I bet you'll look STUNNING X
    Good Luck Gwen and ENJOY x
    
    Feb 24, 2024
  2. Tony80
    What’s the outfit for the evening?
    
    Feb 24, 2024
  3. Gwen Sissymittens
    It was pretty conservative. Heels, leggings, loose blouse, wig...got laughed at by a few people which hurt a little
    
    Feb 25, 2024
    
    Rimmer69 likes this.
8. LoriB
  Glad you liked my response Gwen. I am so happy she is understanding and helping you become a woman. How did it feel to be dressed for three days? Did she take you out shopping for more feminine things?
  
  Jan 7, 2024
  
  Gwen Sissymittens likes this.
  1. Gwen Sissymittens
    You’re welcome. She took me shopping the day before the three days. It was an awesome but tiring experience!
    
    Jan 7, 2024
9. LoriB
  Good for her you need to spend more time in your feminine clothes not less
  
  Jan 6, 2024
  
  KristenDresses, Gwen Sissymittens and TangoSub like this.
10. Gwen Sissymittens
  Earlier I suggested getting out of my female clothes in order to clean faster. My wife simply said no. It was so hot!!!
  
  Jan 5, 2024
  
  KristenDresses, Stephplayswithyou, Aspire02 and 1 other person like this.
11. Gwen Sissymittens
  First of three full maid days down. It was an awesome experience but my dogs are barking!
  
  Jan 4, 2024
  
  KristenDresses, TangoSub, Stephplayswithyou and 1 other person like this.
  1. TangoSub
    One of the best things is being worn out from work on "maid days"!
    
    Jan 5, 2024
    
    Gwen Sissymittens likes this.
12. Gwen Sissymittens
  My wife just informed me that I'll be spending three full days next week as the maid!
  
  Dec 31, 2023
  
  KristenDresses, Rimmer69, John and 5 others like this.
  1. Twila
    Happy for you
    
    Dec 31, 2023
    
    Gwen Sissymittens likes this.
  2. TangoSub
    Very happy for you. Must be a lot of cleaning to get done! :-)
    
    Jan 2, 2024
    
    Gwen Sissymittens likes this.
13. Gwen Sissymittens
  Locked, dressed, and feeling sexy AF!
  
  Sep 3, 2023
  
  KristenDresses, Twila, Teagirl and 3 others like this.
14. Gwen Sissymittens
  Locked in chastity and fully feminized for the first time in months. It feels great!
  
  Jun 6, 2023
  
  KristenDresses, LoriB and Stephplayswithyou like this.
  1. charlottejaneuk
    it always is wondefultobe locked agian
    
    Jun 8, 2023
15. Gwen Sissymittens
  I wore the cutest polka dot stockings to work today!
  
  Jun 5, 2023
  
  KristenDresses and TangoSub like this.
16. Gwen Sissymittens
  @Mistress ComDom really treated me tonight to some wonderful girly things!!!
  
  Jun 5, 2023
  
  KristenDresses and jemima like this.
17. Gwen Sissymittens
  Thanks @DonnaSue for telling @Mistress ComDom about the KTB. It arrived today. It is excruciatingly painful if you’ve never experienced it!
  
  Mar 30, 2023
  
  Ms. Joanne, Rita, DonnaSue and 1 other person like this.
  1. jemima
    well i hope you ok and dont have it lots on you.
    
    Mar 31, 2023
    
    Gwen Sissymittens likes this.
  2. Rita
    perhaps a little iodine could soothe it
    
    Mar 31, 2023
    
    Gwen Sissymittens likes this.
18. Gwen Sissymittens
  @Mistress ComDom rode me for 20 minutes without release. It's an "incentive" to be better on my diet. Then she made me order a KBT.
  
  Mar 29, 2023
  1. View previous comments...
  2. Mistress ComDom
    @Ms. Joanne yes it is the spiky kind!
    
    Mar 30, 2023
    
    Ms. Joanne likes this.
  3. Ms. Joanne
    @Mistress ComDom Oh how deliciously vicious. There will be tears and screams. :)
    
    Mar 30, 2023
    
    Mistress ComDom and Gwen Sissymittens like this.
  4. LockedSissyHusband
    You lucky sissy gwen!
    
    Apr 2, 2023
    
    Gwen Sissymittens likes this.
19. Gwen Sissymittens
  @Mistress ComDom has informed me that the cage stays on until I lose 6 pounds.
  
  Mar 14, 2023
  
  KristenDresses, Mistress ComDom and TangoSub like this.
20. Gwen Sissymittens
  I am locked in my cage, dressed like a slut, and waiting for @Mistress ComDom to get home.
  
  Mar 13, 2023
  
  KristenDresses and Aspire02 like this.
21. Gwen Sissymittens
  Yesterday @Mistress ComDom gave me my maintenance spanking while teasing me at the same time. It was a very painful experience!
  
  Mar 4, 2023
  
  KristenDresses, Goddess Jade and emily chelsea like this.
  1. TangoSub
    I am sure the kind and throughtful Mistress Comdom did it with the best intentions and used it as teaching moment.
    
    Mar 4, 2023
    
    Gwen Sissymittens, Goddess Jade and emily chelsea like this.
22. Gwen Sissymittens
  I just slipped my work clothes on over my emerald green thong, bralette, garter belt, and silky green stockings. Off to work. Life is good!
  
  Mar 2, 2023
  
  KristenDresses, Stephplayswithyou, Mistress ComDom and 1 other person like this.
23. Gwen Sissymittens
  I’m happy that my new genderswap story is #6 on Amazon and that Mistress gave me a surprise O yesterday while in my sexy lingerie! Good days
  
  Feb 24, 2023
  
  KristenDresses, Aspire02 and Stephplayswithyou like this.
24. Gwen Sissymittens
  Three hours full femme today for chore day (pictures in album). @Mistress ComDom declined to removed my chastity cage after chore day.
  
  Feb 18, 2023
  
  KristenDresses, Maid Denise and Aspire02 like this.
  1. Goddess Jade
    Yay!
    
    Feb 18, 2023
    
    Gwen Sissymittens likes this.
25. Gwen Sissymittens
  Just received my maintenance spanking from Mistress...ouch!
  
  Feb 6, 2023
  
  emily chelsea, sissy_kendle and Miss Bella like this.
  1. Miss Bella
    Aw comon, Gwen! no one is buying the ‘ouch’ like you didn’t love it !
    
    Feb 6, 2023
    
    Gwen Sissymittens and Mistress ComDom like this.
  2. Rectrix
    Lucky you, make sure you thank her.
    
    Feb 6, 2023
    
    Gwen Sissymittens and Mistress ComDom like this.
  3. Mistress ComDom
    Oh it was fun...I laughed the whole time I was making her ass so red!
    
    Feb 6, 2023
    
    Gwen Sissymittens likes this.
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About
Gender:

Male

My key is held by:

@Mistress ComDom
Your chastity role:

Submissive

Sissy

Slave

Maid
Chastity devices:

Holy Trainer (v.4)

Chastity resume:

My wife Mistress ComDom and I are pretty new to chastity (started intermittently in 2021), but we are looking to make it a regular part of our daily routine. I came out to my wife as a submissive CD in October 2022 and she has been amazingly supportive and indulgent!
Interact
Content:

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